


FF #9: Sleepless Nights

by CJ_fics



Series: Olicity Flash Fic Challenge [8]
Category: Arrow (TV 2012)
Genre: F/M, Fluff, Smitten Oliver, olicity - Freeform
Language: English
Status: Completed
Published: 2014-12-25
Updated: 2014-12-25
Packaged: 2018-03-03 10:44:08
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,284
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2848076
Author URL: https://archiveofourown.org/users/CJ_fics/pseuds/CJ_fics
Summary: <blockquote class="userstuff">
              <p>When Oliver asks Felicity out on a date, she wants him to be sure -- and ask her again in five days.</p>
            </blockquote>





	FF #9: Sleepless Nights

On the first night, Oliver thinks back about how he got into this situation in the first place.  
  
He had finally, after months of admitting to himself that his feelings for Felicity were more than platonic, gathered up the nerve to ask her out on a date. They were at the new lair, looking for situations Arrow needed to handle. It was a slow night. And he finally blurted out the question he’s been wanting to ask her. Felicity, being Felicity Smoak, doesn’t react as expected.  
  
"Are you sure, Oliver?" she had asked. Her brows scrunched up, and then she starts a massive babble, "I need you to be sure because this is coming out of nowhere. I think so anyway. I know we’ve kind of been hanging out and all of that but this is huge! Huge! You’re asking me out on a date with you! And maybe you’re just lonely or something. Not that I think you can’t find company when, if, you need one. I’m sure there are other women who would love to go out on a date with you. So need to be desperate and all. I mean, I know you’re kind of not as rich as you were before — Not that I’m saying that women only go out with you for your money! I don’t mean that, at all. But you know, maybe you’re feeling less confident about asking other women out now that your funds are limited. But I’m sure perfectly lovely women would love to still go out with you. I mean, just for your face. You’re very good looking. And your body is … Three, two, one. OK, ignore that part. My point is that I’m not the only woman left in your life, Oliver. So you don’t need to ask me out on a date. There are other women, who I’m sure would love to date you, Oliver. So you have to be sure. I—"  
  
"I’m sure, Felicity," he interrupted her, trying to comprehend everything she had said. "I’m not being desperate. I’m not asking you out because I’m lonely. I don’t have insecurities about my lack of funds. I’m sure, like you said, women would still go out with me. I—"  
  
"Good! Great! Ask them out!" she exclaimed making a move to gather her bags.   
  
"Are you saying ‘No’, Felicity?" He tried to sound not pathetic. He thinks he was half-successful. _Maybe she’ll go out with him out of pity? He’ll take that._  
  
"Uhh. I’m not sure," she started. "This is a big deal, Oliver. What about Team Arrow? If—"  
  
"Let’s not call ourselves Team Arrow, please."  
  
"— we go out and it tanks, I don’t want it to affect the team dynamics. This is a smaller lair, so any tension between any of us would be right in everyone’s faces. And the work that we do for the city is very important, Oliver. I don’t think that we should let anything get in the way of that. And Digg! What would he think? I mean, we are his closest friends. And with Little Diggle on her way, he and Lyla need all our support. So, if we go out and it doesn’t work, it would be very uncomfortable and we won’t be able to give as much support to them as we could, if we let things be as they are."  
  
"So you’re saying ‘No’," he stated. He could hear himself. He sounded dejected.  
  
"No, Oliver!" She came closer to him to grasp his forearm. She shook it and said, "I’m saying that you need to be sure. Why are you asking me?"  
  
"Because I’m kinda totally in love with you, Felicity," he said with all the conviction in his bones. He reached for her hand on his forearm, "I want to see where this will go. I want to try. I want to be in that kind of relationship with you, Felicity Smoak. And a date sounds like a good place to start."  
  
 _Please, let her say ‘Yes’ now and put him out of his misery._  
  
She looked shocked at his declaration. She was silent for a bit, gathering her thoughts and waiting for the blush on her cheeks to subside before she takes a deep breath and decides, “Ask me again in five days, Oliver. I need for you to be sure. Because we’re not two strangers meeting for the first time. Our lives are so intertwined as it is. You’re my friend. I’m yours. We work together in Team Arrow — I’m not going to stop calling us that! — and I don’t want to stop working with you. So I need you to be sure. Can you wait five days?”  
  
"Why five days?"  
  
"Five is my favourite prime number."  
  
"All right. I’ll take it. It’s better than five months or five years. Not that I won’t wait that long for you, Felicity. It’s just, five days is better. I’ll ask you again in five days. I promise."  
  
He pecks her cheek and lets her go.  
  
Now, he’s in his apartment, trying and failing to sleep. That conversation playing on a loop in his head.  
  
 _As far as sleepless nights go, this is one of his best._  
  
—————————————-  
  
On the second night, he goes through ideas about what to do when Felicity finally agrees to go out on a date with him.   
  
Yes, his funds are limited, but he’s not destitute. He has managed to save all of his ‘earnings’ from working for A.R.G.U.S. in a separate, secret bank account. He had kept that as back-up, just in case, he needed to rebuild his life and start anew. He has spent most of it outfitting the new lair, paying for lawyers to get his family company back, and paying for his apartment. There’s a considerable amount left, of course, but until he gets QC back, he’s not going to be able to afford any extravagant expenses. Like whisking Felicity off to Paris or a Star Trek convention on a private plane for their first date. Or renting out all of Table Salt for a night so they can have a private dinner.   
  
_Maybe, that invitation to the charity gala?_ As Oliver Queen, he is still significant enough in the Starling City social scene to warrant invitations to charity events. While everyone knew that he wouldn’t be able to afford such generous donations, most event organisers know that whispers of him attending some event would get a lot more people interested and a lot more press coverage.   
  
He quickly dismisses that idea. He doesn’t want to spend his first date with Felicity in the public eye — in uncomfortable clothes. He wants to see her relaxed and not feel self-conscious.   
  
_Dinner and movie?_ Hmm. Might be the kind of relaxed evening that would work. But then again, they have done that as friends over the last few months.  
  
 _Fancy dinner, private movie?_ He can book them a good spot in Table Salt and then rent out a cinema to watch the latest blockbuster. But then, that’s has been his go-to dating move. It’s straight out of the Oliver Queen Playbook. _No, Felicity deserves something better._  
  
 _Picnic in the park?_ The Queen family has donated a lot to the Starling City Park over the last few decades so he knows he can still call in a few favours from the park administration. _He’s never done that for a date. So yeah, that’s something to keep in mind_.  
  
 _Drive-in movie outside the city?_ There’s this new retro drive-in theatre that’s just opened outside of Starling City. Felicity told him about it. She seemed excited about the idea. Definitely worth considering. Maybe dinner on the way, popcorn and drinks on the back of the car and then drive-in movie with Felicity. _Would be the perfect scenario for a proper, retro make out. Hmm._  
  
 _Cook her dinner?_ That’s another idea. He can go to her place or invite her over his, and cook her a nut-free dinner. Problem was, the only things he could cook were mac  & cheese and pancakes. And grilled pheasant and rabbits and forest rats and snakes. He shudders. No, she wouldn’t like him grilling things for her. But still, maybe he could make the effort to learn to cook something she likes. She would definitely appreciate it. A nice three-course meal.  
  
 _Or maybe, their first date could be a weekend trip to the woods outside of Starling City?_ But would that be too presumptuous? Does Felicity even like camping? He’ll have to ask Digg.  
  
By the time he finished thinking the possibilities through, it was five a.m.  
  
 _Another sleepless night. But so worth it._  
  
————————————————-  
  
The third night, he spends trying out recipes for the meal he plans to prepare for Felicity. Stuffed mushrooms for starters. Duck L’orange with potato au gratin for main. Chocolate cupcakes with homemade mint chip ice cream for dessert.  
  
The stuffed mushrooms were a breeze. The duck was a bit tough but he knew he just needed to have it in the oven longer. The chocolate cupcakes exploded in the oven. But the ice cream machine was worth every penny he spent on it.  
  
 _He spends the rest of the night cleaning up his kitchen._  
  
——————————————————  
  
On the fourth night, he begs Capt. Lance to send the Arrow on patrol somewhere in the city. Well, no, not really begged. He determinedly and aggressively asked the captain to allow him to take a section of the city to watch for the night. Thankfully, the captain agreed.  
  
 _He spends most of the night, thinking about how Felicity would taste when he kisses her for the first time._  
  
——————————————————-  
  
The fifth day had finally come, and he was prepared. All he needed to do was to wait for Felicity to come to the lair tonight so he can convince her, using everything at his disposal, that he was sure, that he loved her, and that he wanted to start a true romantic relationship with her.  
  
When she didn’t make it by eight p.m., he started to worry. He checked his phone. No messages. No missed calls. He checked his email. Nothing. He checked her Facebook page. No updates. He calls Diggle. The man didn’t know anything. Same with Roy.  
  
 _She was avoiding him! It’s not that she didn’t believe that he was unsure, it was that she didn’t want to go out with him — and didn’t know how to let him down easy._  
  
The thought pissed him off. They were friends! If she didn’t want to date him, she should tell him. She should know that she could trust him — with everything, even his own disappointment.   
  
_What if she was playing games with him? Wanting him to beg her for a chance? Wanting him to wait for her? It was more than he deserved._  
  
 _Well, if that’s the case, he was going to head over to her place and give him a piece of his mind._  
  
It takes him another two hours to knock on her door. He had been waiting outside her place, leaning against his Ducati, running things over and over again in his head. He needed to calm down and think about his reactions to whatever reason she didn’t show up at the lair tonight. If she was unsure of him, then he would try to convince her. If she was playing games, he was going to kiss her so hard and so deeply that all thoughts of playing games with him would fly out of her head.  
  
 _The point is, whatever her reasons, tell her that you will wait for her to be ready but try not to sound so pathetic._ With that thought in mind, he knocks on her door.  
  
It takes a while to answer. When she does, she doesn’t look like herself. She’s wearing a very loose t-shirt that looks like one of the grey shirts he used to wear in the foundry, plaid flannel pyjamas, her hair in a hornets nest on top of her head, her nose all red, her eyes swollen, her cheeks pale, and her lips dry.  
  
"Felicity?"  
  
"Oliver," she groans, her voice all growly and thick. "What are you doing here?"  
  
"You didn’t show up at the lair. I was waiting for you."  
  
"Did something happen?" she asks as she steps back into her townhouse, motioning for him to follow her.   
  
"No. I was worried."  
  
"I’m sick."  
  
"I can see that. You should have told me or Diggle or Roy."  
  
"Sorry, I just passed out after work today. I think it’s the flu."  
  
"Let’s get you back to bed, Felicity," he says, picking her up in his arms to carry her back to her room. She snuggles against him, almost falling back asleep against his chest.  
  
As he was tucking her in, she wakes up groggily and says, “It’s Day Five.”  
  
"I know," he smiles at her, stroking her hair and her forehead.   
  
"Did you wait long?"  
  
"I waited four sleepless nights and about twenty-two hours today."  
  
"Sorry. I—"  
  
"Felicity, stop. I can wait until you’re better. In fact, I can wait until you’re ready and sure."  
  
She smiles and closes her eyes, snuggling deeper into her pillow, “Will you stay?”  
  
He smiles and kisses her forehead, and then climbs into bed with her, “Always.”  
  
He knows that he won’t get much sleep tonight, taking care of Felicity. It’s his fifth Felicity-induced sleepless night in a row. He doesn’t mind. He’d gladly endure more sleepless nights like this.   
  
_Much better to lack sleep because of your dream than to do so because of your nightmares._  
  
In the morning, he wakes up to her watching him. Smiling, she says, “Yes.”

**Author's Note:**

> Original post: http://outoftheclosetshipper.tumblr.com/post/91748744668/ff-9-sleepless-nights


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